$ 360.0

Quantity: 10Gram

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SKU: 8240004 Category:


Product name: Fmoc-Pra-OH

Synonym: Nα-Fmoc-S-Pra-OH,Fmoc-L-2-propargylglycine,Fmoc-L-Propargylglycine,Fmoc-propargyl-Gly-OH, (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-ynoic acid, (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pent-4-ynoic acid,

Catalog #: 8240004

Purity: 97%

CAS No.: 198561-07-8

Molecular Formula: C20H17NO4

Molecular Weight: 335.35

Compound ID: 2734461

Description: The Pra residue serves as a handle for selective labeling of the bicyclic peptide via click chemistry. The solid-phase assembly of the linear precursor including ε-azido norleucine and the propargylglycine (Pra) in positions i and i+4, resp., was accomplished by either subjecting the resin-bound peptide to selective on-resin diazo transformation of a Lys into the Nle(ε-N3) or the incorporation of Fmoc-Nle(ε-N3)-OH during the stepwise build-up of the resin-bound peptide. A general method for the solid-phase synthesis of carboxy-functionalized peptides by oxidative cleavage of alkynes is presented. Clean and quantitative conversion is enabled by the addition of bases, such as DABCO and HMTA, to the classical OsO4/NaIO4. CuAAC of 8 with Fmoc-Pra-OH 9 (synthesized using published methods(12)) using CuSO4 (20% mol) and NaAsc (40% mol) in DCM/H2O/tBuOH (1:1:1) with microwave irradiation (100 W, 70 °C)(13) afforded the desired building block 6 in 85% yield after purification.